Enantioselective Synthesis of (-)-Basiliskamide A

被引:11
作者
Chen, Ming [1 ]
Roush, William R. [1 ]
机构
[1] Scripps Florida, Dept Chem, Jupiter, FL 33458 USA
基金
美国国家卫生研究院;
关键词
PD/C-CATALYZED HYDROGENATION; BASILISKAMIDE-B; COUPLING REACTIONS; DEPROTECTION; CONVERSION; ALDEHYDES; REAGENTS; ALCOHOLS; ETHERS; ESTER;
D O I
10.1021/ol300282e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Basiliskamide A is an antifungal polyketide natural product isolated by Andersen and co-workers from a Bacillus laterosporus isolate, PNG-276. A nine-step enantioselective synthesis of (-)-basiliskamide A is reported, starting from commercially available beta-hydroxy ester 7. The synthesis features a highly diastereoselective mismatched double asymmetric delta-stannylallylboration reaction of aldehyde 5 with the bifunctional allylborane reagent 4.
引用
收藏
页码:1556 / 1559
页数:4
相关论文
共 30 条
[1]   Tupuseleiamides and basiliskamides, new acyldipeptides and antifungal polyketides produced in culture by a Bacillus laterosporus isolate obtained from a tropical marine habitat [J].
Barsby, T ;
Kelly, MT ;
Andersen, RJ .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (10) :1447-1451
[2]   Coupling reactions of cephalosporin sulfones: A stable 3-stannylated cephem [J].
Buynak, JD ;
Vogeti, L ;
Chen, HS .
ORGANIC LETTERS, 2001, 3 (19) :2953-2956
[3]   Enantioselective Synthesis of (E)-δ-Stannyl Homoallylic Alcohols via Aldehyde Allylboration Using α-Stannylallylboranes Generated by Allene Hydroboration Followed by a Highly Diastereoselective 1,3-Boratropic Shift [J].
Chen, Ming ;
Ess, Daniel H. ;
Roush, William R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (23) :7881-+
[4]   Formal Synthesis of (+)-Sorangicin A [J].
Crimmins, Michael T. ;
Haley, Matthew W. ;
O'Bryan, Elizabeth A. .
ORGANIC LETTERS, 2011, 13 (17) :4712-4715
[5]  
Denmark S.E., 2000, MODERN CARBONYL CHEM, P299
[6]   Catalytic enantioselective addition of allylic organometallic reagents to aldehydes and ketones [J].
Denmark, SE ;
Fu, JP .
CHEMICAL REVIEWS, 2003, 103 (08) :2763-2793
[7]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[8]   Total synthesis of (-)-basiliskamide B [J].
Dias, Luiz C. ;
Goncalves, Caroline da Costa S. .
ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (7-8) :1017-1021
[9]   Total Synthesis of (-)- Basiliskamide A and NMR Studies on the Conversion of Basiliskamide A to Basiliskamide B [J].
Dias, Luiz C. ;
Goncalves, Caroline C. S. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2010, 21 (10) :2012-2016
[10]   Synthesis of isofagomine and a new C6 pyrrolidine azasugar with potential biological activity [J].
Espeel, Pieter E. R. ;
Piens, Kathleen ;
Callewaert, Nico ;
Van der Eycken, Johan .
SYNLETT, 2008, (15) :2321-2325